Hydrochloric Acid → 2-Methoxy-3'-carboethoxy-[1,1'-biphenyl]-6-carboxylic acid, ethyl ester

HRID 275172Notes

Reaction equation

HRID 275172 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([OH:11])=[O:10])[C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:13]=1.Cl.[CH3:24][CH2:25]OC(C)=O.CCCCCC>CCO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([O:11][CH2:24][CH3:25])=[O:10])[C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 152329332-Methoxy-3'-carboethoxy-[1,1'-biphenyl]-6-carboxylic acidHCID 21226206Ethyl acetate hexane

Product 1

HCID 867484752-Methoxy-3'-carboethoxy-[1,1'-biphenyl]-6-carboxylic acid, ethyl esterYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acid 5a (0.583 g., 1.90 mmol, 1 equiv.) is dissolved in 12 mL of absolute EtOH. Concentrated HCl (0.6 mL) is added, and the mixture heated to reflux for 24 hours. The mixture is then partitioned between EtOAc and water. The organic phase is washed with brine, dried (MgSO4), and concentrated in vacuo. Chromatography on silica gel using 5%, then 10% EtOAc/hexane yields 2-methoxy-3'-carboethoxy-[1,1'-biphenyl]-6-carboxylic acid, ethyl ester (6a) (0.432 g., 1.32 mmol, 73%) as a clear oil: UVmax (CHCl3) 242 nm (ε=12036), 296 nm (ε=4724); 1H NMR (300 MHz, CDCl3) δ 8.01 (m, 1H, ArH), 7.92 (m, 1H, ArH), 7.47-7.40 (m, 3H, ArH), 7.39 (dd, J=8, 8 Hz, 1H, ArH), 7.09 (dd, J= 2, 8 Hz, 1H, ArH), 4.34 (q, J=7 Hz, 2H, CO2CH2), 3.98 (q, J=7 Hz, 2H, CO2CH2), 3.73 (s, 3H, OCH3), 1.35 (t, J=7 Hz, 3H, CH2CH3), 0.91 (t, J=7 Hz, 3H, CH2CH3); 13C NMR (75 MHz, CDCl3) δ 168.04 (C=O), 166.65 (C=O), 156.92, 137.28, 134.11, 133.22, 130.73, 130.07, 129.98, 128.78, 128.22, 127.63, 121.63, 113.87, 60.88, 56.02, 14.34, 13.65; IR (film) 2982, 1718, 1466, 1366, 1298, 1260, 1234, 1110, 1060 cm-1 ; MS (DCI) m/e 329 (MH+), 283 (M--C2H5O). Anal. Calcd for C19H20O5 : C, 69.50; H, 6.14. Found: C, 69.44; H, 6.19.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 24 hours
  3. customThe mixture is then partitioned between EtOAc and water
  4. washThe organic phase is washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6443cfb4ba7241ae96d486ebe5db8617
Source dataset
uspto-grants-1995_02
Patent number
US05391817

Reaction notes

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